Doc Love: Dating An Older Woman

This week, Doc Love advises a young reader on how to date an older woman.

Reader's Question

Hey Doc,

I’m a longtime reader, and I think what you’re doing to help joes like us is awesome.

Here’s my situation. I met Claudine at work. She seems like my type of girl — sarcastic and slightly jaded on the outside, though I can tell she’s a big softy like me on the inside. We see each other in the workplace, but we don’t actually work with each other, so there isn’t really that dating-a-coworker problem.

No Playing Games

Here are my two issues. First, I’m usually really good at hooking the girl, but I’ve had trouble with reeling them in, so to speak. I’m the type of guy who doesn’t really like playing games, and I let women know who I am straight out because I figure if they don’t like me for me, then there’s no point in dating them, and it’s just wasted time. I play cocky, but I’m a big softy on the inside. I’ve gotten mixed results; most girls really dig it, but some haven’t. So I guess what I’m asking is, how should I approach the first date with Claudine?

An Older Woman

Secondly, there’s the age difference between us. I’m 20, and Claudine’s 25. I’m kind of worried that the age difference might come into play here. I can’t foresee anything specific, because she doesn’t seem like a bar diver or a party girl. My friends and I can get pretty goofy, but she seems to really like me for my goofy self. Also, what can a 20-year-old and a 25-year-old do on a first date that would be fun? Any ideas?

Lace — who’s just getting back into the game

Doc Love's Response

Hi Lace,

First of all, how do you know this girl is a big softy on the inside? You only see her at work, you’ve never taken her out, and you’ve never even sat down and talked to her for an hour. Heck, you don’t know the first thing about her except for her name and where she works! Like the great Doctor Freud once said: “You’re just projecting here.”

Also, how do you know Claudine’s not a bar diver or a party girl? You’ve never even been out with her! You’ve judged this girl, and you know nothing whatsoever about her — she’s a complete stranger to you.

And “reeling them in” is exactly what my techniques are all about. Most guys can get a girl to like them at the beginning, but that’s where it ends. They can’t keep them, or as you say, “reel them in.” That’s where “The System” comes in — and that’s why you need my book. In those pages, you’ll get every technique you need to hook and land a woman, and keep her for the long run.

So what are you waiting for, Lace?

To Be Or Not To Be Honest

Now, this whole thing about letting women know who you are, warts and all, is a complete pile of garbage. To you psych majors: You don’t tell a girl on the first date that you rob banks. Like my cousin Fast Eddie Love from East L.A. says: “You tell her after she falls in love with you. Then she can’t leave.” You’re not supposed to give her any negatives whatsoever. Like my cousin Sal “The Fish” Love says: “At the beginning, it’s a cat-and-mouse game.” So when you tell me you’re completely up-front with women, I know right then and there you don’t know the first thing about them.